5,8,10-Heptadecatrienoic acid, 12-hydroxy-, (S)-

Base Information

• Chemical Name: 5,8,10-Heptadecatrienoic acid, 12-hydroxy-, (S)-
• CAS No.: 64234-42-0
• Molecular Formula: C₁₇H₂₈O₃
• Molecular Weight: 280.408
• European Community (EC) Number: 633-391-7
• Nikkaji Number: J410.721G,J2.564.026H,J1.779.334I
• Wikipedia: 12-Hydroxyheptadecatrienoic_acid
• Mol file: 64234-42-0.mol

Synonyms:5,8,10-Heptadecatrienoic acid, 12-hydroxy-, (S)-;64234-42-0;54397-84-1;(12S)-12-Hydroxy-5,8,10-heptadecanetrienoic acid;(5E,8E,10E,12S)-12-Hydroxy-5,8,10-heptadecatrienoic acid;(5Z,8E,10E,12S)-12-Hydroxy-5,8,10-heptadecatrienoic acid

Chemical Property of 5,8,10-Heptadecatrienoic acid, 12-hydroxy-, (S)-

Chemical Property:

• Vapor Pressure: 4.64E-10mmHg at 25°C
• Boiling Point: 451.8°C at 760 mmHg
• Flash Point: 241.1°C
• Density: 0.992g/cm³
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 12
• Exact Mass: 280.20384475
• Heavy Atom Count: 20
• Complexity: 316

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC(C=CC=CCC=CCCCC(=O)O)O
• Isomeric SMILES: CCCCC[C@@H](/C=C/C=C/C/C=C/CCCC(=O)O)O

Technology Process of 5,8,10-Heptadecatrienoic acid, 12-hydroxy-, (S)-

There total 80 articles about 5,8,10-Heptadecatrienoic acid, 12-hydroxy-, (S)- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

(5Z,8E,10E,12S)-12-hydroxy-5,8,10-heptadecatrienoic acid methyl ester (79171-56-5) → 12-HHT (50683-78-8,54397-84-1,64234-42-0)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; water;

DOI:10.1055/s-0033-1338961

Reference yield: 90.0%

C33H46O3Si → C17H28O3 (54397-84-1,64234-42-0)

Guidance literature:

With tetrabutyl ammonium fluoride;

DOI:10.1055/s-0033-1338961

Reference yield:

all cis 5,8,11,14-eicosatetraenoic acid (506-32-1,236743-58-1) → Malondialdehyde (542-78-9) + (5Z,8Z,10Z)-12-Hydroxy-heptadeca-5,8,10-trienoic acid (50683-78-8,54397-84-1,64234-42-0)

Guidance literature:

With calcimycin; disodium hydrogenphosphate; potassium dihydrogenphosphate; platelet suspension of pig blood; In water; dimethyl sulfoxide; at 37 ℃; Kinetics; Mechanism; also with additives;

DOI:10.1002/(SICI)1521-4184(199811)331:11<359::AID-ARDP359>3.0.CO;2-B

upstream raw materials:

(R)-1ξ-iodo-oct-1-en-3-ol

ester methylique du 12-HHT

all cis 5,8,11,14-eicosatetraenoic acid

(5Z,8E,10E,12S)-12-hydroxy-5,8,10-heptadecatrienoic acid methyl ester

Downstream raw materials:

hydroxyheptadeca-5Z,8E,10E-trienoicacid

Refernces

• 1、 Tojo, Toshifumi,Wang, Qian,Okuno, Toshiaki,Yokomizo, Takehiko,Kobayashi, Yuichi. "Synthesis of (S,5 Z,8 E,10 E)-12-hydroxyheptadeca-5,8,10-trienoic acid (12 S -HHT) and its analogues". . p. 1545 - 1548. Retrieved 2013/08/23.
• 2、 John,Schlegel. "Thermodynamic and structural characterization of cis-trans isomerization of 12-(S)-hydroxy-(5Z, 8E,10E)-heptadecatrienoic acid by high-performance liquid chromatography and gaschromatography-mass spectrometry". . p. 181 - 188. Retrieved 2007/10/03.